ES2271137T3 - Procedimiento para la preparacion de alcoholes dibencilicos sustituidos con halogenos. - Google Patents

Procedimiento para la preparacion de alcoholes dibencilicos sustituidos con halogenos. Download PDF

Info

Publication number: ES2271137T3
Authority: ES; Spain
Prior art keywords: acid; general formula; acids; halogenated; mol
Prior art date: 2001-04-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES02006615T

Other languages

English (en)

Spanish (es)

Inventor

Lars Dr. Rodefeld

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lanxess Deutschland GmbH

Original Assignee

Lanxess Deutschland GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-04-06

Filing date

2002-03-25

Publication date

2007-04-16

2002-03-25 Application filed by Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH

2007-04-16 Application granted granted Critical

2007-04-16 Publication of ES2271137T3 publication Critical patent/ES2271137T3/es

2022-03-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 32
238000002360 preparation method Methods 0.000 title claims description 28
229910052736 halogen Inorganic materials 0.000 title claims description 21
150000002367 halogens Chemical group 0.000 title claims description 19
150000001298 alcohols Chemical class 0.000 title description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 43
150000003504 terephthalic acids Chemical class 0.000 claims abstract description 20
239000002168 alkylating agent Substances 0.000 claims abstract description 18
229940100198 alkylating agent Drugs 0.000 claims abstract description 18
229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 claims abstract description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
-1 halogenated dibenzyl alcohols Chemical class 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000003960 organic solvent Substances 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims description 46
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 11
239000011737 fluorine Substances 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
WFNRNCNCXRGUKN-UHFFFAOYSA-N 2,3,5,6-tetrafluoroterephthalic acid Chemical compound OC(=O)C1=C(F)C(F)=C(C(O)=O)C(F)=C1F WFNRNCNCXRGUKN-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical class N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 claims description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
150000008050 dialkyl sulfates Chemical class 0.000 claims description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
KZCBXHSWMMIEQU-UHFFFAOYSA-N Chlorthal Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(C(O)=O)C(Cl)=C1Cl KZCBXHSWMMIEQU-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 claims 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 claims 1
239000003880 polar aprotic solvent Substances 0.000 claims 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 7
235000011149 sulphuric acid Nutrition 0.000 abstract 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 13
239000000243 solution Substances 0.000 description 12
238000004821 distillation Methods 0.000 description 11
PCRSJGWFEMHHEW-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-dicarbonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(F)=C1C#N PCRSJGWFEMHHEW-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
239000002917 insecticide Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003905 agrochemical Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000008096 xylene Substances 0.000 description 2
AGWVQASYTKCTCC-UHFFFAOYSA-N (2,3,5,6-tetrafluorophenyl)methanol Chemical compound OCC1=C(F)C(F)=CC(F)=C1F AGWVQASYTKCTCC-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
KVLBXIOFJUWSJQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzoic acid Chemical class OC(=O)C1=C(F)C(F)=CC(F)=C1F KVLBXIOFJUWSJQ-UHFFFAOYSA-N 0.000 description 1
IOQMWOBRUDNEOA-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzonitrile Chemical compound FC1=CC(F)=C(F)C(C#N)=C1F IOQMWOBRUDNEOA-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
BBWGBNSBAMWIEK-UHFFFAOYSA-N CC1(F)CC(F)=C(F)C(N)(N)C1(C)F Chemical compound CC1(F)CC(F)=C(F)C(N)(N)C1(C)F BBWGBNSBAMWIEK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
ZKIBBIKDPHAFLN-UHFFFAOYSA-N boronium Chemical compound [H][B+]([H])([H])[H] ZKIBBIKDPHAFLN-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000010411 cooking Methods 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Tropical Medicine & Parasitology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

ES02006615T 2001-04-06 2002-03-25 Procedimiento para la preparacion de alcoholes dibencilicos sustituidos con halogenos. Expired - Lifetime ES2271137T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10117206		2001-04-06
DE10117206A DE10117206A1 (de)	2001-04-06	2001-04-06	Verfahren zur Herstellung von halogensubstituierten Dibenzylalkoholen, diese halogensubstituierten Dibenzylalkohole sowie deren Verwendung

Publications (1)

Publication Number	Publication Date
ES2271137T3 true ES2271137T3 (es)	2007-04-16

Family

ID=7680650

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES02006615T Expired - Lifetime ES2271137T3 (es)	2001-04-06	2002-03-25	Procedimiento para la preparacion de alcoholes dibencilicos sustituidos con halogenos.

Country Status (7)

Country	Link
US (1)	US6759558B2 (de)
EP (1)	EP1247792B1 (de)
JP (1)	JP2002332251A (de)
CN (1)	CN1225442C (de)
AT (1)	ATE335716T1 (de)
DE (2)	DE10117206A1 (de)
ES (1)	ES2271137T3 (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL153511A0 (en) *	2000-07-04	2003-07-06	Showa Denko Kk	Production method for benzenedimethanol compound
JP4685779B2 (ja) *	2003-10-10	2011-05-18	江蘇揚農化工股▲ふん▼有限公司	ピレスロイド化合物の合成中間体の製造方法
JP4815926B2 (ja) *	2004-08-05	2011-11-16	住友化学株式会社	ハロゲン置換ベンゼンジメタノールの製造方法
DE602005025497D1 (de) *	2004-08-05	2011-02-03	Sumitomo Chemical Co	Verfahren zur herstellung von halogensubstituiertem benzoldimethanol
JP5029000B2 (ja) *	2006-01-10	2012-09-19	住友化学株式会社	ハロゲン置換ベンゼンジメタノールの製造法
HUP0800566A3 (en) *	2006-01-10	2010-08-30	Sumitomo Chemical Co	Method for producing halogen-substituted benzenedimethanol
JP5233123B2 (ja) *	2006-01-24	2013-07-10	住友化学株式会社	ハロゲン置換ベンゼンジメタノールの製法
ATE517075T1 (de) *	2006-01-24	2011-08-15	Sumitomo Chemical Co	Verfahren zur herstellung von halogensubstituiertem benzoldimethanol
CN101479221B (zh) *	2006-06-27	2013-01-16	住友化学株式会社	卤素取代苯二甲醇的制备方法
CN101973850B (zh) *	2010-08-31	2013-04-03	上海赫腾精细化工有限公司	2,3,5,6-四氟对苯二甲醇的制备方法
CN103641686B (zh) *	2013-12-09	2015-07-01	连云港市华通化学有限公司	2,3,5,6-四氟-1,4-对苯二甲醇的合成方法
CN104892356B (zh) *	2015-05-08	2017-10-17	常州市阳光药业有限公司	间三氟甲基苯丙醇的制备方法
CN114835558A (zh) *	2022-04-22	2022-08-02	苏州亚科科技股份有限公司	一种2,3,5,6-四氟对苯二甲醇的制备工艺

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2631168A (en) *	1948-02-07	1953-03-10	Sprague Electric Co	Polyfunctional halogenated aromatic compounds and condensation products thereof
US3029290A (en) *	1958-04-30	1962-04-10	Diamond Alkali Co	Ring-substituted halo alpha, alpha'-xylene-ols
US4140843A (en) *	1967-01-16	1979-02-20	Ciba-Geigy Ag	Nuclear halogenated α,α'-bis(cyclopentadienyl)xylene
US4107104A (en) *	1970-09-09	1978-08-15	Ethyl Corporation	Halogenated xylenes
US3899466A (en) *	1970-09-09	1975-08-12	Ethyl Corp	Brominated xylene diols
DE2345233A1 (de) *	1973-09-07	1975-03-27	Dynamit Nobel Ag	Herstellung von tetrachlor-xylylenglykolen
US4141912A (en) *	1973-10-29	1979-02-27	Hooker Chemicals & Plastics Corp.	Process for the preparation of polyhalobenzylic disulfooxonium compounds
DE2825362A1 (de) *	1978-06-09	1979-12-13	Dynamit Nobel Ag	Verfahren zur herstellung von benzylalkoholen durch decarbonylierung von ameisensaeureestern
GB2127013B (en) *	1982-09-17	1985-12-11	Ici Plc	Tetrafluoroterephthalyl alcohol esters thereof and a process for their preparation
GB8403548D0 (en) *	1984-02-10	1984-03-14	Ici Plc	Chemical process
DE3714602A1 (de) *	1987-05-01	1988-11-10	Bayer Ag	Verfahren zur herstellung von 2,3,5,6-tetrafluor-benzyl-alkoholen
GB8718620D0 (en)	1987-08-06	1987-09-09	Ici Plc	Insecticide compounds
GB9126677D0 (en) *	1991-12-16	1992-02-12	Johnson Matthey Plc	Improvements in chemical compounds
JP4135215B2 (ja)	1997-12-03	2008-08-20	住友化学株式会社	ピレスロイド化合物及びそれを有効成分とする害虫防除剤
JPH11335331A (ja)	1998-05-22	1999-12-07	Sumitomo Chem Co Ltd	ピレスロイド化合物および該化合物を含有する害虫防除剤
AU754206B2 (en)	1998-06-09	2002-11-07	Sumitomo Chemical Company, Limited	Ester compounds
US6624336B1 (en)	1999-05-07	2003-09-23	Showa Denko K.K.	Process for producing tetrafluorobenzenemethanols
DE10003320C2 (de)	2000-01-27	2002-04-11	Bayer Ag	Verfahren zur Herstellung von 2,3,5,6-Tetrahalogen-xylylidenverbindungen
IL153511A0 (en) *	2000-07-04	2003-07-06	Showa Denko Kk	Production method for benzenedimethanol compound

2001
- 2001-04-06 DE DE10117206A patent/DE10117206A1/de not_active Withdrawn
2002
- 2002-03-25 DE DE50207758T patent/DE50207758D1/de not_active Expired - Lifetime
- 2002-03-25 AT AT02006615T patent/ATE335716T1/de not_active IP Right Cessation
- 2002-03-25 EP EP02006615A patent/EP1247792B1/de not_active Expired - Lifetime
- 2002-03-25 ES ES02006615T patent/ES2271137T3/es not_active Expired - Lifetime
- 2002-04-01 JP JP2002098577A patent/JP2002332251A/ja active Pending
- 2002-04-05 US US10/117,523 patent/US6759558B2/en not_active Expired - Fee Related
- 2002-04-05 CN CNB021054622A patent/CN1225442C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP2002332251A (ja)	2002-11-22
EP1247792B1 (de)	2006-08-09
US6759558B2 (en)	2004-07-06
DE50207758D1 (de)	2006-09-21
CN1225442C (zh)	2005-11-02
DE10117206A1 (de)	2002-10-10
HK1051031A1 (en)	2003-07-18
EP1247792A3 (de)	2003-10-29
EP1247792A2 (de)	2002-10-09
CN1380275A (zh)	2002-11-20
US20020156330A1 (en)	2002-10-24
ATE335716T1 (de)	2006-09-15

Publication	Publication Date	Title
ES2965853T3 (es)	2024-04-17	Sulfonación de alcanos sin disolventes
ES2222743T3 (es)	2005-02-01	Procedimiento para preparar un derivado 4-trifluorometilsulfinilpirazol.
CA1290764C (en)	1991-10-15	Preparation of sulphonated aromatic esters
ES2998512T3 (en)	2025-02-20	Methods for the preparation of 1,3-benzodioxole heterocyclic compounds
KR101249865B1 (ko)	2013-04-02	인돌린 화합물 및 그 제조방법
ES2961237T3 (es)	2024-03-11	Métodos para la preparación de compuestos heterocíclicos de 1,3-benzodioxol
SE449992B (sv)	1987-06-01	Hydroxilering av aromatiska kolveten
EP3334712B1 (de)	2019-10-09	Neues verfahren zur herstellung von krystalischem methyl n-[2-[[[1-(4-chlorophenyl)-1h-pyrazol-3-yl]oxy]methyl]phenyl]-n-methoxycarbamate
US20140179922A1 (en)	2014-06-26	Intermediate compounds and process for the preparation of lurasidone and salts thereof
ES2624692T3 (es)	2017-07-17	Procedimiento para la preparación de derivados de acrilato de cianofenoxi-pirimidiniloxi-fenilo sustituido
US6759558B2 (en)	2004-07-06	Process for preparing halogen-substituted dibenzyl alcohols, these halogen-substituted dibenzyl alcohols and their use
ES2306493T3 (es)	2008-11-01	Procedimiento para la produccion de 3-hidroxipiperidinas sustituidas.
ES2361239T3 (es)	2011-06-15	Procedimiento de purificación de montelukast.
CN101351438A (zh)	2009-01-21	在合成达菲中的环氧化物中间体
US6864372B2 (en)	2005-03-08	Process for the production of sulfonic esters
ES2302009T3 (es)	2008-07-01	Separacion de un diacetal de glioxal por extraccion liquido-liquido a contracorriente.
ES2302694T3 (es)	2008-08-01	Procedimiento para la preparacion de (1r,2s,4r)-(-)-2-(2'-n,n-dimetilamino-etoxi)-2-fenil-1,7,7-tri-metil-biciclo 2.2.1 heptano y sus sales de adicion de acido farmaceuticamente aceptables.
ES2289406T3 (es)	2008-02-01	Procedimiento para preparar pantoprazol y sus sales.
EP2980079B1 (de)	2017-10-25	Verfahren zur herstellung einer pyridazinonverbindung
ES2217114T3 (es)	2004-11-01	Nuevo procedimiento para la preparacion de alfa-(2,4-disulfofenil)-n-terc-butilnitrona y sales farmaceuticamente aceptables de la misma.
CA1223267A (en)	1987-06-23	Substituted azetidine derivatives, process for their preparation; and their use as intermediates
ES2335488T3 (es)	2010-03-29	Alquilacion estereoselectiva de piperazinas quirales 2-metil-4-protegidas.
ES2235538T3 (es)	2005-07-01	Procedimiento para la preparacion de para-trifluormetilanilinas polihalogenadas.
ES2330890T3 (es)	2009-12-16	Procedimiento para la produccion de carboxanilidas.
KR102814311B1 (ko)	2025-05-28	화합물의 제조방법